2008 Jeep Wrangler

Most Fun for Under $20,000

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The Jeep Wrangler remains a hit by straying little from the original formula: toughness, frugality, and an outcome unforeseen by designers creating a machine for the rigors of war in the first half of the past century—fun.

Unless you are cruising Daytona Beach with your Wrangler bursting with co-eds, the most fun you can have with your Jeep means removing macadam and concrete from the equation. Your Wrangler would rather be ferrying you to vistas unsullied by asphalt and Manifest Destiny.

The beauty of the old technology used in the Wrangler’s suspension and powertrain is that there are fewer gizmos to break, and when things do break, they’re cheaper to fix. Want to make your Wrangler scale ruins like a billy goat or—resplendent in urethane and tubular steel armor—look like it could? Buy one, and you’ll have access to perhaps the largest aftermarket parts selection available for any vehicle in the U.S.

Or, like most owners, you can simply choose to enjoy the Wrangler for the fun-loving and simple beast that it is, ferrying you through the urban wilds that separate your Bikram yoga studio from the sorority house.